(1S)-2,4,7,7-tetramethyl-2-azabicyclo<2.2.1>heptan-3-one | 246044-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1S)-2,4,7,7-tetramethyl-2-azabicyclo<2.2.1>heptan-3-one
• 英文别名: (1S,4R)-2,4,7,7-tetramethyl-2-azabicyclo[2.2.1]heptan-3-one
• CAS: 246044-06-4
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: HIAIOEXLTYPWJM-XVKPBYJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S)-2,4,7,7-tetramethyl-2-azabicyclo<2.2.1>heptan-3-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以58%的产率得到(1S)-2,4,7,7-tetramethyl-2-azabicyclo<2.2.1>heptan-3-thione
  参考文献：
  名称：

  Conformational properties and chiroptical spectra of lactams and thiolactams with 2-azabicyclo[2.2.1]heptane, 2- and 3-azabicyclo[3.2.1]octane skeletons

  摘要：

  The CD spectra of several bicyclic lactams and thiolactams were measured in different solvents. The concentration dependence of the spectra observed in hydrocarbon solvents was attributed to shifts in the equilibrium between monomer and hydrogen-bonded dimer forms. The CD of some compounds is characterized by unusually strong Cotton effects resulting from non-planarity of the amide bonds due to internal strain of the bicyclic skeletons. The X-ray crystallographic structures of 2a,c, 3b,d and 4a,b showed different degrees of distortion of the amide or thioamide moieties from planarity, which causes inherent chirality of the chromophores and profoundly affects the Cotton effect sign and magnitude. This distortion also restricts application of the sector rules for prediction of the n-pi* CD sign, since they can be used only for compounds with planar chromophores. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00262-1
• 作为产物：
  描述：

  (1S)-4,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one 、 碘甲烷 在 sodium hydride 作用下， 生成 (1S)-2,4,7,7-tetramethyl-2-azabicyclo<2.2.1>heptan-3-one
  参考文献：
  名称：

  Conformational properties and chiroptical spectra of lactams and thiolactams with 2-azabicyclo[2.2.1]heptane, 2- and 3-azabicyclo[3.2.1]octane skeletons

  摘要：

  The CD spectra of several bicyclic lactams and thiolactams were measured in different solvents. The concentration dependence of the spectra observed in hydrocarbon solvents was attributed to shifts in the equilibrium between monomer and hydrogen-bonded dimer forms. The CD of some compounds is characterized by unusually strong Cotton effects resulting from non-planarity of the amide bonds due to internal strain of the bicyclic skeletons. The X-ray crystallographic structures of 2a,c, 3b,d and 4a,b showed different degrees of distortion of the amide or thioamide moieties from planarity, which causes inherent chirality of the chromophores and profoundly affects the Cotton effect sign and magnitude. This distortion also restricts application of the sector rules for prediction of the n-pi* CD sign, since they can be used only for compounds with planar chromophores. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00262-1

文献信息

• Chiroptical spectra of bicyclic selenolactams. Optical activity of the singlet–triplet transition
  作者：Maria J Milewska、Tadeusz Połoński

  DOI：10.1016/s0957-4166(99)00444-9

  日期：1999.10

  Two selenolactams with rigid 2-azabicyclo[2.2.1]heptane skeletons were prepared by reaction of the corresponding lactams with P4Se10. A comparison of their UV-vis and CD spectra with those of the carbonyl and thiocarbonyl analogues showed a similar character of the lowest-energy electronic transitions and the same signs of the corresponding Cotton effects. The MCD spectra of selenolactams revealed that their n-pi* absorption band is dominated by the singlet-triplet component. A very weak CD corresponding to this component has an opposite sign to its much stronger singlet-singlet counterpart observed at the blue edge of the n-pi* band. (C) 1999 Elsevier Science Ltd. All rights reserved.